Isopropylamine → Esatenolol

HRID 1107057ノート

反応式

HRID 1107057 の反応式
[C:1]([CH2:4][C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][CH:11]2[O:13][CH2:12]2)=[CH:7][CH:6]=1)(=[O:3])[NH2:2].[CH:16]([NH2:19])([CH3:18])[CH3:17]>CO>[CH3:17][CH:16]([NH:19][CH2:12][C@H:11]([OH:13])[CH2:10][O:9][C:8]1[CH:14]=[CH:15][C:5]([CH2:4][C:1]([NH2:2])=[O:3])=[CH:6][CH:7]=1)[CH3:18]

参加物

4

反応物 2

HCID 6363IsopropylamineHCID 1198572-(4-(2,3-Epoxypropoxy)phenyl)acetamide

生成物 1

HCID 175540Esatenolol収率 70.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
10 °C

実験手順

P-Hydroxyphenylacetamide (1 g) and (S)-glycidyl p-toluenesulfonate (1.51 g, 99.3% e.e.) were dissolved in acetone (30 ml). Potassium carbonate (1.19 g) was added to the solution and stirred for 30 hours under refluxing. After the reaction, inorganic materials were filtered off and acetone was removed to give 1.43 g of crude (S)-1-[p-(carbamoylmethyl)phenoxy-2,3-epoxypropane. Then, crude (S)-1-[p-(carbamoylmethyl)phenoxy-2,3-epoxypropane (1.43 g) was dissolved in methanol (8 ml). The solution was dropped in isopropylamine (6.8 g) under cooling to 10° C. over a period of 1 hour and the reaction temperature was raised to room temperature and stirred for 7 hours. After the reaction, the mixture was condensed in vacuo until crystals beginning to separate, cooled, filtrated by suction and dried in vacuo to give crude (S)-atenolol (1.29 g). The optical purity of it was 62.8% e.e. by measurement of Chiral column OD (Daisel Chemical industries Ltd.).

後処理

  1. temperaturethe reaction temperature was raised to room temperature
  2. customAfter the reaction
  3. customcondensed in vacuo until crystals
  4. customto separate
  5. temperaturecooled
  6. filtrationfiltrated by suction
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-8489f136fb044bed8b4bbc3ff88869ab
出典データセット
uspto-grants-2000_05
特許番号
US06057476

反応ノート

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